Potassium Hydroxide → HCID 66571366, compound

HRID 534189Notes

Reaction equation

HRID 534189 reaction equation
FC(F)(F)C([N:5]([CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[OH-].[K+]>CO.O>[CH3:25][S:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][NH:5][C@@H:6]2[CH2:8][C@H:7]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:17][CH2:18]1)(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86708245HCID 86708245, compound

Product 1

HCID 66571366HCID 66571366, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-((1-(methylsulfonyl)piperidin-4-yl)methyl)-N-((trans)-2-phenylcyclopropyl)acetamide (150 mg, 0.37 mmol) in a mixture of MeOH (6 mL) and H2O (4 mL) was added KOH (62 mg, 1.11 mmol) at 0° C. stirred for 2 h rt. Reaction mixture was concentrated and the residue was dissolved in water (10 mL) and acidified with 50% HCl and washed with ethyl acetate (2×10 mL). The aqueous layer was basified with saturated sodium carbonate solution and extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with water (25 mL), brine (25 mL) and dried over anhydrous Na2SO4 and concentrated under the reduced pressure to obtain the desired product (trans)-N-((1-(methylsulfonyl)piperidin-4-yl)methyl)-2-phenylcyclopropanamine (57 mg, 51.8%) as colourless gummy oil. HPLC-97.64%, m/z 309.35 (M+H)+. H1NMR (CDCl3) δ ppm 7.23-7.25 (m, 2H), 7.16-7.13 (m, 1H), 7.02 (d, J=7.2 Hz, 2H), 3.81 (d, J=11.2 Hz, 2H), 2.76 (s, 3H), 2.60-2.66 (m, 4H), 2.30-2.34 (m, 1H), 1.82-1.88 (m, 3H), 1.52-1.56 (m, 2H), 1.29-1.36 (m, 2H), 0.95-1.06 (m, 2H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in water (10 mL)
  4. washwashed with ethyl acetate (2×10 mL)
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. washThe combined organic layer was washed with water (25 mL), brine (25 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-884e108c267448d48167f7cbe6186110
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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